My TV is a 2009 Ford F150 SCREW 5.4L 4x4 with factory tow package and Hopkins “Agility” brake controller. The profile as is sits pretty level to the eye. However, I know I’m running max on the weight carrying capacity of the hitch of 5000/500. I've been reading a lot on the Reese WDH’s and thinking I'll be going to go that route based on reviews and price. The problem is I'm racking my brains on how high of a rating I should go to.

Any insight on how I should evaluate my particular needs? What would you experienced guys recommend? 6000/600 or higher? How high is too high? What Reese set-up with sway control would you recommend? Should I even bother getting one yet? Run it as is and see how it goes?

That's OK. I love my well-proven Equal-i-zer, but I still watch it for problems.
Anderson is not yet proven by time. It's worth watching, in case issues pop up, or other couplers are shown to be sensitive.